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2C-B: Difference between revisions
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==History and culture== | ==History and culture== | ||
2C-B was first synthesized and tested for psychoactivity in 1974 by [[Alexander Shulgin]], who was in search of novel psychedelic compounds based on the chemical structure of mescaline. His findings were later published in his 1991 book [[PiHKAL]], in which it was listed among the "magical half-dozen" of [[psychedelic]] [[phenethylamines]] that he deemed most important.<ref name="PiHKAL"/> The list consists of [[mescaline]], [[DOM]], [[2C-B]], [[2C-E]], [[2C-T-2]], and [[2C-T-7]].<ref>{{cite book|title=PiHKAL: A Chemical Love Story|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|url=https://erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref> In interviews, Alexander Shulgin repeatedly declared it his favorite psychedelic trip.<ref>{{cite magazine|url=https://www.scientificamerican.com/article/self-experimenter-chemist-explores-new-psychedelics/|title=Self-Experimenters: Psychedelic Chemist Explores the Surreality of Inner Space, One Drug at a Time|author=David Biello|date=March 20, 2008|issn=0036-8733|eissn=1946-7087|magazine=Scientific American|publisher=Nature Publishing Group|access-date=October 10, 2020}}</ref> | 2C-B was first synthesized and tested for psychoactivity in 1974 by [[Alexander Shulgin]], who was in search of novel psychedelic compounds based on the chemical structure of mescaline. His findings were later published in his 1991 book [[PiHKAL]], in which it was listed among the "magical half-dozen" of [[psychedelic]] [[phenethylamines]] that he deemed most important.<ref name="PiHKAL" /> The list consists of [[mescaline]], [[DOM]], [[2C-B]], [[2C-E]], [[2C-T-2]], and [[2C-T-7]].<ref>{{cite book|title=PiHKAL: A Chemical Love Story|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|url=https://erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref> In interviews, Alexander Shulgin repeatedly declared it his favorite psychedelic trip.<ref>{{cite magazine|url=https://www.scientificamerican.com/article/self-experimenter-chemist-explores-new-psychedelics/|title=Self-Experimenters: Psychedelic Chemist Explores the Surreality of Inner Space, One Drug at a Time|author=David Biello|date=March 20, 2008|issn=0036-8733|eissn=1946-7087|magazine=Scientific American|publisher=Nature Publishing Group|access-date=October 10, 2020}}</ref> | ||
In the 1970s, 2C-B was used in patients by a small number of psychotherapists in the United States. These therapists reported that it created a warm, empathetic bond between them and their patients, helping to break down their ego defenses and inner resistances and allowing the patient to get in touch with suppressed emotions and repressed memories.<ref>{{cite web|url=http://www.encyclopedia.com/science/applied-and-social-sciences-magazines/2c-b-nexus|title=2C-B (Nexus)|website=Encyclopedia.com|access-date=October 10, 2020}}</ref> The gentle nature of 2C-B, in addition to its mild side effects and short duration, were found to be desirable traits for a therapeutic setting. | In the 1970s, 2C-B was used in patients by a small number of psychotherapists in the United States. These therapists reported that it created a warm, empathetic bond between them and their patients, helping to break down their ego defenses and inner resistances and allowing the patient to get in touch with suppressed emotions and repressed memories.<ref>{{cite web|url=http://www.encyclopedia.com/science/applied-and-social-sciences-magazines/2c-b-nexus|title=2C-B (Nexus)|website=Encyclopedia.com|access-date=October 10, 2020}}</ref> The gentle nature of 2C-B, in addition to its mild side effects and short duration, were found to be desirable traits for a therapeutic setting. | ||
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Shortly after gaining traction in the underground psychotherapy community, 2C-B became popular in the recreational drug scene. 2C-B was well-liked as a [[MDMA]] substitute in raves and parties due to its minimal comedown and a clear, euphoric headspace. In the 1980s and early 1990s, several foreign companies legitimately manufactured 2C-B under the brand names "Nexus", "Erox", and "Performax" and advertised that it would alleviate impotence, frigidity, and diminished libido. It was sold at adult book and video stores, "head" shops, and some nightclubs. The DEA reported its distribution in Miami, Florida as yellow pills marketed as an aphrodisiac.{{citation needed}} | Shortly after gaining traction in the underground psychotherapy community, 2C-B became popular in the recreational drug scene. 2C-B was well-liked as a [[MDMA]] substitute in raves and parties due to its minimal comedown and a clear, euphoric headspace. In the 1980s and early 1990s, several foreign companies legitimately manufactured 2C-B under the brand names "Nexus", "Erox", and "Performax" and advertised that it would alleviate impotence, frigidity, and diminished libido. It was sold at adult book and video stores, "head" shops, and some nightclubs. The DEA reported its distribution in Miami, Florida as yellow pills marketed as an aphrodisiac.{{citation needed}} | ||
In the United States, 2C-B gained popularity as an alternative to MDMA following its classification as a Schedule I substance in 1985. Its increasing popularity led it to be placed in Schedule I in 1995.<ref name="DEA2001"/> It saw a resurgence in interest in the 2000s, with the advent of the research chemicals scene and darknet markets. | In the United States, 2C-B gained popularity as an alternative to MDMA following its classification as a Schedule I substance in 1985. Its increasing popularity led it to be placed in Schedule I in 1995.<ref name="DEA2001" /> It saw a resurgence in interest in the 2000s, with the advent of the research chemicals scene and darknet markets. | ||
2C-B was legally sold in Southern Africa from 1993 to early 1996. It was marketed as medicine for Sangomas (traditional healers) under the name "Ubulawu Nomathotholo", which roughly translates to "Medicine of the Singing Ancestors".<ref>{{cite web|url=http://www.tacethno.com/info/2cb/2cbhistory.html#South%20Africa |title=History of Nexus|website=Tacethno.com|date=March 27, 2008|access-date=May 15, 2012}}{{Dubious}}</ref><ref>{{cite web|url=http://www.erowid.org/chemicals/2cb/2cb_article1.shtml|title=The Nexus Factor: An Introduction to 2C-B|publisher=Erowid|author="Anu"|date=February 1996|access-date=October 10, 2020|orig-year=Modified 2016}}</ref><ref>{{cite AV media|url=http://www.erowid.org/chemicals/show_image.php?i=2cb/ubulawu_pack.jpg|title=Ubulawu Nomathotholo Package|publisher=Erowid|year=2002|medium=Picture}}</ref> | 2C-B was legally sold in Southern Africa from 1993 to early 1996. It was marketed as medicine for Sangomas (traditional healers) under the name "Ubulawu Nomathotholo", which roughly translates to "Medicine of the Singing Ancestors".<ref>{{cite web|url=http://www.tacethno.com/info/2cb/2cbhistory.html#South%20Africa |title=History of Nexus|website=Tacethno.com|date=March 27, 2008|access-date=May 15, 2012}}{{Dubious}}</ref><ref>{{cite web|url=http://www.erowid.org/chemicals/2cb/2cb_article1.shtml|title=The Nexus Factor: An Introduction to 2C-B|publisher=Erowid|author="Anu"|date=February 1996|access-date=October 10, 2020|orig-year=Modified 2016}}</ref><ref>{{cite AV media|url=http://www.erowid.org/chemicals/show_image.php?i=2cb/ubulawu_pack.jpg|title=Ubulawu Nomathotholo Package|publisher=Erowid|year=2002|medium=Picture}}</ref> | ||
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2C-B, or 2,5-dimethoxy-4-bromophenethylamine, is a [[substituted phenethylamine]]. Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure, a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-B possesses methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a bromine atom attached to carbon R<sub>4</sub> of the phenyl ring. | 2C-B, or 2,5-dimethoxy-4-bromophenethylamine, is a [[substituted phenethylamine]]. Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure, a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-B possesses methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a bromine atom attached to carbon R<sub>4</sub> of the phenyl ring. | ||
2C-B belongs to the [[2C-x|2C family]] of phenethylamines, all of which possess methoxy groups on the 2 and 5 positions of the benzene ring.<ref name="PiHKAL"/> | 2C-B belongs to the [[2C-x|2C family]] of phenethylamines, all of which possess methoxy groups on the 2 and 5 positions of the benzene ring.<ref name="PiHKAL" /> | ||
==Pharmacology== | ==Pharmacology== | ||
{{pharmacology}} | {{pharmacology}} | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
Unlike most [[psychedelic]]s, 2C-B has been shown to be a low efficacy [[serotonin]] 5-HT<sub>2A</sub> receptor [[Agonist#Agonists|partial agonist]]<ref name="Moya2007">{{cite journal|title=Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives at Human 5-Hydroxytryptamine (5-HT)<sub>2A</sub> and 5-HT<sub>2C</sub> Receptors|first1=P. R.|last1=Moya|first2=K. A.|last2=Berg|first3=M. A.|last3=Gutiérrez-Hernandez|first4=P.|last4=Sáez-Briones|first5=M.|last5=Reyes-Parada|first6=B. K.|last6=Cassels|first7=W. P.|last7=Clarke|journal=Journal of Pharmacology and Experimental Therapeutics|year=2007|volume=321|issue=3|pages=1054-1061|doi=10.1124/jpet.106.117507|issn=0022-3565|eissn=1521-0103|oclc=1606914|pmid=17337633}}</ref> or even full [[antagonist]].<ref>{{cite journal|title=4‐Bromo‐2,5‐dimethoxyphenethylamine (2C‐B) and structurally related phenylethylamines are potent 5‐HT<sub>2A</sub> receptor antagonists in Xenopus laevis oocytes|volume=141|issue=7|year=2004|pages=1167-1174|first1=C. A.|last1=Villalobos|first2=P.|last2=Bull|first3=P.|last3=Sáez|first4=B. K.|last4=Cassels|first5=J. P.|last5=Huidobro‐Toro|doi=10.1038/sj.bjp.0705722|pmc=1574890|pmid=15006903|doi-access=free|journal=British Journal of Pharmacology|eissn=1476-5381|issn=0007-1188|oclc=01240522}}</ref> This suggests that the 5-HT<sub>2C</sub> receptor is primarily responsible for mediating the effects experienced by users of 2C-B.<ref name="Moya2007"/> Research also suggests that 2C-B increases [[dopamine]] levels in the brains of rats which may contribute to its psychoactivity.<ref>{{cite journal|last1=Páleníček|first1=T.|last2=Fujáková|first2=M.|last3=Brunovský|first3=M.|first4=J.|last4=Horáček|first5=I.|last5=Gorman|first6=M.|last6=Balíková|first7=L.|last7=Rambousek|first8=K.|last8=Syslová|first9=P.|last9=Kačer|first10=P.|last10=Zach|first11=V.|last11=Bubeníková-Valešová|first12=F.|last12=Tylš|first13=A.|last13=Kubešová|first14=J.|last14=Puskarčíková|first15=C.|last15=Höschl|title=Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats|journal=Psychopharmacology|volume=225|pages=75–93|year=2013|doi=10.1007/s00213-012-2797-7|pmid=22842791|issn=0033-3158|eissn=1432-2072|oclc=2409222}}</ref> | Unlike most [[psychedelic]]s, 2C-B has been shown to be a low efficacy [[serotonin]] 5-HT<sub>2A</sub> receptor [[Agonist#Agonists|partial agonist]]<ref name="Moya2007">{{cite journal|title=Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives at Human 5-Hydroxytryptamine (5-HT)<sub>2A</sub> and 5-HT<sub>2C</sub> Receptors|first1=P. R.|last1=Moya|first2=K. A.|last2=Berg|first3=M. A.|last3=Gutiérrez-Hernandez|first4=P.|last4=Sáez-Briones|first5=M.|last5=Reyes-Parada|first6=B. K.|last6=Cassels|first7=W. P.|last7=Clarke|journal=Journal of Pharmacology and Experimental Therapeutics|year=2007|volume=321|issue=3|pages=1054-1061|doi=10.1124/jpet.106.117507|issn=0022-3565|eissn=1521-0103|oclc=1606914|pmid=17337633}}</ref> or even full [[antagonist]].<ref>{{cite journal|title=4‐Bromo‐2,5‐dimethoxyphenethylamine (2C‐B) and structurally related phenylethylamines are potent 5‐HT<sub>2A</sub> receptor antagonists in Xenopus laevis oocytes|volume=141|issue=7|year=2004|pages=1167-1174|first1=C. A.|last1=Villalobos|first2=P.|last2=Bull|first3=P.|last3=Sáez|first4=B. K.|last4=Cassels|first5=J. P.|last5=Huidobro‐Toro|doi=10.1038/sj.bjp.0705722|pmc=1574890|pmid=15006903|doi-access=free|journal=British Journal of Pharmacology|eissn=1476-5381|issn=0007-1188|oclc=01240522}}</ref> This suggests that the 5-HT<sub>2C</sub> receptor is primarily responsible for mediating the effects experienced by users of 2C-B.<ref name="Moya2007" /> Research also suggests that 2C-B increases [[dopamine]] levels in the brains of rats which may contribute to its psychoactivity.<ref>{{cite journal|last1=Páleníček|first1=T.|last2=Fujáková|first2=M.|last3=Brunovský|first3=M.|first4=J.|last4=Horáček|first5=I.|last5=Gorman|first6=M.|last6=Balíková|first7=L.|last7=Rambousek|first8=K.|last8=Syslová|first9=P.|last9=Kačer|first10=P.|last10=Zach|first11=V.|last11=Bubeníková-Valešová|first12=F.|last12=Tylš|first13=A.|last13=Kubešová|first14=J.|last14=Puskarčíková|first15=C.|last15=Höschl|title=Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats|journal=Psychopharmacology|volume=225|pages=75–93|year=2013|doi=10.1007/s00213-012-2797-7|pmid=22842791|issn=0033-3158|eissn=1432-2072|oclc=2409222}}</ref> | ||
However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive. | However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive. | ||
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===Cardiac risk=== | ===Cardiac risk=== | ||
Users have reported | Users have reported experiencing hypertension, hyperthermia and tachycardia at higher doses.<ref>{{cite journal|title=Acute Pharmacological Effects of 2C-B in Humans: An Observational Study|journal=Frontiers in Pharmacology|volume=9|page=206|year=2018|doi=10.3389/fphar.2018.00206|pmc=5859368|pmid=29593537|issn=1663-9812|doi-access=free|first1=E.|last1=Papaseit|first2=M.|last2=Farré|first3=C.|last3=Pérez-Mañá|first4=M.|last4=Torrens|first5=M.|last5=Ventura|first6=M.|last6=Pujadas|first7=R.|last7=de la Torre|first8=D.|last8=González|oclc=1198838203}}</ref> As such, those with pre-existing heart conditions should avoid using 2C-B, and users monitor their temperature and heart-rate and respond accordingly. Heavy physical exertion while on 2C-B is discouraged. | ||
===Lethal dosage=== | ===Lethal dosage=== | ||
There is no current data for the LD<sub>50</sub> of 2C-B, but it is thought to be considerably higher than the active dose. [[Alexander Shulgin]] reported a 100 mg oral dose taken without apparent harm.<ref name="PiHKAL"/> | There is no current data for the LD<sub>50</sub> of 2C-B, but it is thought to be considerably higher than the active dose. [[Alexander Shulgin]] reported a 100 mg oral dose taken without apparent harm.<ref name="PiHKAL" /> | ||
===Dependence and abuse potential=== | ===Dependence and abuse potential=== | ||
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==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Psychedelic]] | *[[Psychedelic]] | ||